N-aroylamino acid amides as endothelin inhibitors

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 207/327 (2006.01) A61K 31/18 (2006.01) A61K 31/33 (2006.01) A61K 38/05 (2006.01) C07C 311/51 (2006.01) C07D 213/56 (2006.01) C07D 213/81 (2006.01) C07D 261/08 (2006.01) C07D 295/155 (2006.01) C07D 309/28 (2006.01) C07D 333/24 (2006.01) C07D 401/12 (2006.01) C07D 403/12 (2006.01) C07D 405/12 (2006.01) C07D 405/14 (2006.01) C07D 409/12 (2006.01) C07D 409/14 (2006.01) C07D 411/12 (2006.01) C07D 413/12 (2006.01) C07D 417/12 (2006.01) C07K 5/065 (2006.01)

Patent

CA 2218716

The present invention relates to the compounds of formula (I) wherein R is carboxy, esterified carboxy, carbamoyl, N-(alkyl or aryl)-carbamoyl, cyano, 5- tetrazolyl or CONH-SO2-R4; R1 is hydrogen, lower alkyl, aryl-lower alkyl or cycloalkyl-lower alkyl; R2 is hydrogen or lower alkyl, or R1 and R2 represent lower alkylene to form together with the carbon and nitrogen atoms to which they are attached an azacycloalkane ring; R3 is heterocyclic or carbocyclic (aryl or biaryl)-lower alkyl; Y is lower alkylidenyl, 3- to 10-membered cycloalkylidenyl which may be substituted by oxo, alkylenedioxy, hydroxy, acyloxy, lower alkoxy; or Y is 5- to 10-membered cycloalkylidenyl fused to a saturated or unsaturated carbocyclic 5- or 6-membered ring; or Y is 5- to 8- membered oxacycloalkylidenyl, 5- to 8-membered (thia-, oxothia- or dioxothia-) cycloalkylidenyl, or 5- to 8-membered azacycloalkylidenyl optionally N- substituted by lower alkyl or aryl-lower alkyl; R4 represents hydrogen, lower alkyl, carbocyclic aryl, heterocyclic aryl, cycloalkyl, (carbocyclic aryl, heterocyclic aryl, cycloalkyl, hydroxy, acyloxy, or lower alkoxy)-lower alkyl, lower alkyl substituted by carboxyl, by esterified carboxyl or by amidated carboxyl; Ar represents carbocyclic or heterocyclic aryl; and pharmaceutically acceptable salts thereof; which are useful as endothelin inhibitors in mammals.

Composés de formule (I) dans laquelle R est carboxy, carboxy estérifié, carbamoyle, N-(alkyle ou aryle)-carbamoyle, cyano, 5-tétrazolyle ou CONH-SO¿2?-R¿4?; R¿1? est hydrogène, alkyle inférieur, aryle-alkyle inférieur ou cycloalkyle-alkyle inférieur; R¿2? est hydrogène ou alkyle inférieur ou R¿1? et R¿2? représentent alkylène inférieur pour former ensemble un cycle azacycloalcane avec les atomes de carbone et d'azote auxquels ils sont accolés; R¿3? est (aryle ou biaryle)-alkyle inférieur hétérocyclique ou carbocyclique; Y est alkylidényle inférieur, cycloalkylidényle ayant de 3 à 10 éléments, qui peut être substitué par oxo, alkylènedioxy, hydroxy, acyloxy, alcoxy inférieur, ou Y est cycloalkylidényle ayant de 5 à 10 éléments condensé avec un cycle saturé ou insaturé carbocyclique à 5 ou 6 éléments, ou Y est oxacycloalkylidényle ayant de 5 à 8 éléments, (thia-, oxothia- ou dioxothia-) cycloalkylidényle ayant de 5 à 8 éléments, ou azacycloalkylidényle ayant 5 à 8 éléments, éventuellement à substitution N par alkyle inférieur ou aryle-alkyle inférieur; R¿4? représente hydrogène, alkyle inférieur, aryle carbocyclique, aryle hétérocyclique, cycloalkyle, (aryle carbocyclique, aryle hétérocyclique, cycloalkyle, hydroxy, acyloxy ou alcoxy inférieur)-alkyle inférieur, alkyle inférieur substitué par carboxyle, par carboxyle estérifié ou par carboxyle amidé, Ar représente aryle carbocyclique ou hétérocyclique; et sels pharmaceutiquement acceptables desdits composés, utiles en tant qu'inhibiteurs d'endothéline chez les mammifères.

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